Still with me? Great! So, here we go.
1)- SUSPENSION. This was my main problem with the TW, and also one of my favorite things about it. What? Huh? Yeah! The suspension on my TW was poor for higher speed off-roading, but it allowed a low seat height and comfy ride on fire roads. See? Good and bad. I frequently bottomed the suspension riding on whoop trails. My next step with the TW was to try some stiffer pro cycle springs, but I decided that I'd never be able to truly fix it due to the short travel. So, the WRR definitely wins this category for my style of riding. The WRR suspension seems great so far. Yeah the shock may need some tuning, but it's long travel (11") and soaks up bumps nicely. I can easily carry quite a bit more speed when the trail gets rough. This suspension is plush on road, and great offroad too. It's hugely confidence inspiring offroad.
2)- RIDE HEIGHT. This is closely related to suspension, but deserves its own category as its a huge pro for the TW. I'm 5'9" and about 200lbs geared up, 29-30" inseam. The TW was super comfy for me, I could flat foot the bike with bent knees. It was great for slow speed exploration and going "boldly where no rider has gone before." Unfortunately, I didn't do enough of this to justify the performance I was giving up. The WRR has a claimed stock seat height of 36.6 inches, and a tall rear fender. This gets even taller once you replace the stock tires with real knobbies. These combined make it an intimidating machine at first. But, they had to put those 11" of suspension travel somewhere. Once i'm moving past a walking pace, I no longer notice the height. Anyhow, I was able to adjust the shock to bring the bike about an inch lower. But with my aggressive tires, I'm still measuring over 36" at the lowest part of the seat. It works for me, but I have to make sure I stop on level ground, and lean to one side. Similar to how I ride my motocross bikes. I have no plans to lower it further.
3)- ENGINE. Huge win for the WRR, obviously. It's not so much the increase in power, but usability. The WR is fuel injected. This is a huge improvement for me. Ease of starting, less warm up, and ridiculous throttle response. Plus, higher reliability. I know, I know.., I'll address that in a minute. The WR also has a 6 speed wide ratio (get it? WR?) transmission that allows a range of gearing choices. The TW had similar power right off idle (maybe up to 2000 RPM?) and after that the WR pulls away. I frankly was surprised at how powerful the WRR feels. I wasn't expecting much from a four stroke 250 tuned for reliability. I am able to easily spin the rear tire off road, loft the front tire on command, and even steer the bike just with throttle like you would a MX bike. Very fun stuff! The TW and WRR seem to produce a similar exhaust volume, both are nice and quiet stock. The WRR makes less internal engine noises, but it's also newer. The WRR has a 26,800 mile valve service interval. The TW has a backup kick starter, which I miss on the WRR. I'll have to closely monitor the battery.
4)- MAINTENANCE. Tough call. While the TW is a simpler machine, mine was 22 years older than the WR. Consequently, it had been worked on by some people who... Let's just say they shouldn't be working on motorcycles. It was mostly stock, but I was fixing lots of issues due to mismatched hardware and simply age. Rubber and seals wear out. This can't be a negative for all TWs, as many people are riding TWs newer than my 2013 WRR, just mine in particular. My particular WRR still has a several years left on its factory extended warranty. I've never had a motorcycle with a warranty before! But regardless, both bikes are known to be super reliable. They both require regular servicing of chains and tires etc. The WR had a fuel pump failure issue on early 2008 models, but that has since been fixed with a redesigned fuel pump so I don't anticipate any problems. The WRR has more choices in tires due to its more common wheel sizes. If I choose to open up the bike with air box mods and exhaust, I will have to purchase a fuel programmer like the "power commander v" whereas on the TW I'd just buy a handful of jets. So, more expensive but easier. Routine stuff like oil changes are very similar. The WR has almost the exact same oil filter setup as the TW.
5)- ROAD RIDING. This was interesting. My TW was great up to about 45-50mph. 45 was its happy place. It topped out, wide open, around 65 mph. But riding regularly at that speed for me was out of the question. The bike was screaming, and running hot. After high speed runs, I'd see oil weeping out of the cylinder base gasket which never happened when I was kind to the bike. Roads to the woods are 50-55mph speed limited, and cars go faster. I was forever running the slow lane, or pulling into the shoulder and letting cars go around me. You could say that the engine was the limiting factor on the TW. On the WR, it's happy place seems to be around 65mph. I've seen 80, and it still had plenty left. This bike is limited by my tire choice only. Above 75 or so, the front knobby gets a nice speed wobble / wander which is a bit scary. A good set of road tires would prevent this, but that's not my mission as you know. 6th gear is wonderful. The WR is so quiet that wind and tire noise completely blocks the engine out above ~50mph. I wish Yamaha would update the TW with 6th and fuel injection.
6)- LOW SPEED HANDLING. Here, the TW wins hands down. Below 5 mph, the low seat height, low gearing and fat tire balance just make the TW unstoppable. The WR is tall, so it's hard to make a tight offroad u turn in uneven terrain. Also, it has a very abrupt off idle throttle response that is a bit annoying. Several fixes are discussed on the WR forum, I'll report back with which one I choose. Lower gearing (larger rear sprocket) would help here.
7)- GENERAL. I'm really happy with my WRR. It's the plated dirtbike I wanted. It will run fast trails, jump, and slide. I love the fuel injection for ease of use and efficiency. It's great to be on a modern bike again. My TW, being a 1991, had the old handlebar switchgear and no trip meter. Little things but the modern stuff on the WRR, including digital dash with fuel light, is just great to have. I do miss my little tractor TW, and would never have sold it if I could afford to buy the WRR without selling. That being said, I'd like to get another one someday as a companion to my WRR for slow offroad exploration. Different missions, different bikes.